TitleStructural revision of sesbagrandiflorains A and B, and synthesis and biological evaluation of 6-methoxy-2-arylbenzofuran derivatives.
Publication TypeJournal Article
Year of Publication2021
AuthorsNoviany N, Samadi A, Carpenter EL, Abugrain ME, Hadi S, Purwitasari N, Indra G, Indra A, Mahmud T
JournalJ Nat Med
Date Published2021 Jan
KeywordsBenzofurans, Humans, Molecular Structure

Sesbagrandiflorains A (1) and B (2), isolated from the stem bark of the Indonesian fabaceous plant Sesbania grandiflora, were reported to be 6-methoxy-2-(2´,3´-dihydroxy-5´-methoxyphenyl)-1-benzofuran-3-carbaldehyde and 6-hydroxy-2-(2´,3´-dihydroxy-5´-methoxyphenyl)-1-benzofuran-3-carbaldehyde, respectively. However, based on reevaluation of their 1D and 2D NMR data, the chemical structures of 1 and 2 have been revised to 4-hydroxy-2-(4´-hydroxy-2´-methoxyphenyl)-6-methoxybenzofuran-3-carbaldehyde and 4-hydroxy-2-(4´-hydroxy-2´-hydroxyphenyl)-6-methoxybenzofuran-3-carbaldehyde, respectively. In addition, seven new derivatives of 1 have been synthesized from the natural product in good yields (65 - 93%). The chemical structures of the synthetic compounds-one diester (6), four ethers (7-10), one secondary amine (11), and one oxime (12)-were confirmed by MS and NMR analysis. Compound 6 exhibited moderate antibacterial activity against the plant pathogen Rhodococcus fascians with a MIC of 0.1 mg/mL. Compounds 8 and 12 demonstrated respectable cytotoxicity against A375 melanoma cancer cells line with the relative IC values of 22.8 and 32.7 μM, respectively.

Alternate JournalJ Nat Med
PubMed ID32809097
PubMed Central IDPMC7791000
Grant ListPSN Grant 2017-2019 (No. 860/UN26.21/PN/2019), PDUPT Grant 2019 (No. 856/UN26.21/PN/2019) and World Class Professor Program-Scheme B 2018 (No.123.44/D2.3/KP/2018) / / the Directorate of Research and Community Services, Directorate General of Higher Education, The Ministry of Research, Technology and Higher Education, Republic of Indonesia /
T32AT010131 / / the National Center for Complementary & Integrative Health of the National Institutes of Health /
2014-51181-22384 / / the National Institute of Food and Agriculture of the U.S. Department of Agriculture /
#2014162 / / M.J. Murdock Charitable Trust (US) /
HEI Grant 1S10OD018518 / / Foundation for the National Institutes of Health /
S10 OD018518 / OD / NIH HHS / United States
T32 AT010131 / AT / NCCIH NIH HHS / United States